As an artist, Esten has one goal: “to get my music out there into the world.” And so, every Friday, he drops a new song, as part of his Every Single Friday initiative.

“With this, I can’t fail at that [goal]; I’ve automatically won,” Esten tells The Boot. “Now once you do that, anything can happen with a song; anybody on any radio station or any streaming can fall in love with that song. In some sense, it’s like buying a lottery ticket every week.”

Esten, 51, says that he was initially surprised to find out that no one else was doing something like this — until he started realizing the potential pitfalls of sharing his new music.

“Generally, when [someone hasn’t done something], it’s because there’s a reason not to do it, and there’s a number of reasons not to do it,” Esten admits. “Any label will tell you that I’m stepping all over my last single constantly, incessantly, and as soon as something might have a moment to get some air, I’ve got another one coming out, and I get that and that makes sense. But to be honest, I have all this music …”

Esten acknowledges that his Every Single Friday project is a gamble — “First, you need a whole bunch of music to do this … Secondly, you need some sort of fan base itself.” — but it’s a risk he will gladly take, if only to share his songs with his fans. While the star concedes that a record deal might be a possibility down the road, for now, he’s just happy that he has a way to share his music.

“I’m not wide-eyed; I know the thing the industry does to make hits, hits,” Esten notes. “But for right now, it became more important for me, after a long career of acting — where I say what other people tell me to say, I say it the way they direct me to say it, they edit it, they put it out — I just, in some way, wanted to get my voice out there, my music out there, and it sure is doing that.”